Sodium borohydride → HCID 21186580, compound

HRID 1003616Notes

Reaction equation

HRID 1003616 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([C:22](=[O:38])[CH:23]([N:25]2[CH2:30][CH2:29][C:28]([OH:37])([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:27][CH2:26]2)[CH3:24])[CH:7]=[C:8]([F:21])[C:9]=1[O:10][Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13]>C(O)C>[F:3][C:4]1[CH:5]=[C:6]([CH:22]([OH:38])[CH:23]([N:25]2[CH2:26][CH2:27][C:28]([OH:37])([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:29][CH2:30]2)[CH3:24])[CH:7]=[C:8]([F:21])[C:9]=1[O:10][Si:11]([CH:12]([CH3:13])[CH3:14])([CH:15]([CH3:17])[CH3:16])[CH:18]([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21186649HCID 21186649, compound

Product 1

HCID 21186580HCID 21186580, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of sodium borohydride (0.16 g, 4.23 mmol) and ethanol (5 mL) was stirred 10 min and then 1-(3,5-difluoro-4-triisopropylsilyloxyphenyl)-2-(4-hydroxy-4-phenylpiperidin-1-yl)-propan-1-one (1.40 g, 2.86 mmol in 20 mL of ethanol) was added. The reaction was stirred at ambient temperature for 3 days. The reaction was quenched with water and stirred 4 h. The white precipitate which formed was collected by filtration and recrystallized from ethanol to afford 0.46 g (32%) of 1R*,2R*1-(3,5-difluoro-4-triisopropylsilyloxyphenyl)-2-(4-hydroxy-4-phenylpiperidin-1-yl)-propan-1-ol which had: NMR δ 7.54 (d, J=7.5 Hz, 2 H), 7.40 (t, J=7.5 Hz, J=8.5 Hz, 2 H), 7.31 (d, J=7 Hz, 1 H), 6.89 (d, J=9 Hz, 2 H), 5.28 (s, 1 H), 4.18 (d, J=9.5 Hz, 1 H), 3.10 (dt, J=2.2, 11.7 Hz, 1 H), 2.73-2.69 (m, 2 H), 2.62-2.51 (m, 2 H), 2.30-2.06 (m, 2 H), 1.90-1.83 (m, 2 H), 1.36-1.20 (m, 3 H), 1.10 (d, J=7 Hz, 18 H), 0.85 (d, J=6.7 Hz, 3 H). Analysis calculated for C29H43F2NO3Si: C, 67.02; H, 8.34; N, 2.69. Found: C, 66.77; H, 8.58; N, 2.71.

Workup

  1. stirringThe reaction was stirred at ambient temperature for 3 days
  2. customThe reaction was quenched with water
  3. stirringstirred 4 h
  4. customThe white precipitate which formed
  5. filtrationwas collected by filtration
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-8416eba80c2643329b9f2a1b7716b4c8
Source dataset
uspto-grants-2000_04
Patent number
US06046213

Reaction notes

Loading…